The Korean Journal of Pesticide Science (농약과학회지)

The Korean Society of Pesticide Science (한국농약과학회)
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Minimum Structural Requirements of R-phenoxy Substituents for Herbicidal Evaluation of O-(2-phenoxy)ethyl-N-aralkylcarbamate Analogues against Phytoene Desaturase

Phytoene Desaturase에 대한 O-(2-Phenoxy)ethyl-N-aralkylcarbamates 유도체의 제초성 평가를 위한 R-phenoxy 치환기들의 구조적인 요건

  • Choi, Won-Seok (Department of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University) ;
  • Lee, Jae-Whang (Department of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University) ;
  • Hwang, Seung-Woo (Department of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University) ;
  • Sung, Nack-Do (Department of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University)
  • 최원석 (충남대학교 농업생명과학대학 응용생물화학과) ;
  • 이재황 (충남대학교 농업생명과학대학 응용생물화학과) ;
  • 황승우 (충남대학교 농업생명과학대학 응용생물화학과) ;
  • 성낙도 (충남대학교 농업생명과학대학 응용생물화학과)
  • Received : 2010.02.16
  • Accepted : 2010.03.02
  • Published : 2010.03.31
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Abstract

The minimum structural requirements of R-phenoxy substituents for herbicidal evaluation of O-(2-(R)-phenoxy)-ethyl-N-aralkylcarbamate (1-15) analogues against phytoene desaturase (PDS) based on the three dimensional quantitative structure-activity relationships (3D-QSARs: CoMFA and CoMSIA) were studied quantitatively. The correlativity and predictability ($r^2_{cv.}=0.753$ and $r^2_{ncv.}=0.964$) of the CoMFA 1 model were higher than those of the rest models. The PDS inhibitory activities from the optimized CoMFA 1 model were depend upon the steric field (44.0%), electrostatic field (36.3%), and hydrophobic field (19.6%) of O-(2-(R)-phenoxy)ethyl-Naralkylcarbamate analogues. From the CoMFA contour maps on the structure of the most active compound (5), if it has the steric favor at meta-, para-position on the phenoxy ring, the negative charge favor in meta-position and positive charge favor in the outside part of para-position, the inhibitory activity will be predicted to increase. Also, if ortho-, para-position, and outside of phenoxy ring are hydrophilic favor, and meta-position is hydrophobic favor, it is predicted that the inhibitory activity against PDS will be able to increase.

3차원적 정량적인 구조-활성관계(3D-QSARs: CoMFA 및 CoMSIA)에 기초하여 phytoene desaturase (PDS)에 대한 O-(2-phenoxy)ethyl-N-aralkylcarbamate 유도체(1-15)의 제초성 평가를 위한 R-phenoxy 치환기들의 구조적인 요건들을 정량적으로 검토하였다. CoMFA 1 모델의 예측성 및 상관성($r^2_{cv.}=0.753$ 및 $r^2_{ncv.}=0.964$)이 나머지 모델들보다 높았다. 최적화된 CoMFA 1 모델로부터 PDS 저해활성은 O-(2-phenoxy)ethyl-N-aralkylcarbamate 유도체들의 입체장(44.0%), 정전기장(36.3%) 및 소수성장(19.6%)에 의존적이었다. CoMFA 등고도 분석결과, phenoxy 고리상 meta-와 para-위치에는 입체적으로 큰 치환기, meta-위치는 음하전, para-위치의 바깥 부분에는 양하전, ortho- 및 para- phenoxy 고리 중앙의 바깥 부분에는 친수성 치환기가 그리고 meta-위치에 소수성 R-치환기가 각각 도입될 경우에 PDS에 대한 저해활성이 증가할 것으로 예측되었다.

Keywords

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